1445780-92-6Relevant articles and documents
Interaction of tris(3-Hydroxymethyl)phosphine with cinnamic acids
Moiseev, Dmitry V.,James, Brian R.,Gushchin, Aleksey V.
, p. 678 - 690 (2013/07/26)
Phosphonium zwitterions of the known type R3P+CH(Ar)CH2CO2 - (II) are obtained as a racemic mixture in moderate yield via a 1:1 reaction of cinnamic acids (Ar = phenyl, or substituted phenyl) with [HO(CH2)3]3P in acetone at room temperature under Ar. The products are characterized by elemental analysis, 31P{1H}-, 1H-, and 13C{1H}-NMR spectroscopies, and mass spectrometry, although they contain a minor coproduct formed via neutralization of the positive and negative charges of II with the respective acid and phosphine reactants (see Experimental Section). In CD3OD, the monodeuterated salts R3P+CH(Ar)CH(D)CO2 - are formed as a mixture of diastereomers with d.r. values of ~2 to 8, depending on substituent groups present in the organic acid; in these studies, 2-HO-cinnamic acid is the most reactive, and β-methylcinnamic acid is the least reactive.